I know that I am asking a lot of questions. I'm still getting my feet wet.

We're having a problem with MS Exchange 2010 on MS Server 2008R2 and Outlook Anywhere. OWA works just fine inside and outside of the domain. Outlook works just fine inside the domain, but not outside. When somebody does attempt to connect outside, they get the attached error message.

I have rebooted the Exchange server twice now and it seems to only fix the problem temporarily. Does anybody know of a more permanent fix for this problem?

Wife of SAM (interesting name), it is an internal Exchange server that is available outside via a sub-domain for both OWA and Outlook Anywhere (normally).

lol, well SAM responded first...

Okay, I'm hoping a mod moves this to the Exchange board for you so that you get more responses. I do stuff with O365, not so much hosted Exchange.

Some questions that may help with others with troubleshooting your issue:

Are all of the users on Outlook 2010? Have you ever had this error on an internal machine? Are the machines getting the error laptops that are sometimes internal, sometimes external, or completely external users?

Wife of SAM (interesting name), it is an internal Exchange server that is available outside via a sub-domain for both OWA and Outlook Anywhere (normally).

lol, well SAM responded first...

Okay, I'm hoping a mod moves this to the Exchange board for you so that you get more responses. I do stuff with O365, not so much hosted Exchange.

Some questions that may help with others with troubleshooting your issue:

Are all of the users on Outlook 2010? Have you ever had this error on an internal machine? Are the machines getting the error laptops that are sometimes internal, sometimes external, or completely external users?

Moved first to Office forum but went ahead and moved it to Exchange after looking at the error a little more.

Make sure the certificate info in Outlook Anywhere settings match your named server in the certificate. I made a mistake once on my cert and I had to manually change the msstd: reference to match my named server in the cert before Outlook Anywhere would connect properly.

I think I might have found my problem. Before my time, my exchange server was named one thing and is now named something else and OWA was not updated of the fact. Later, a certificate was created for the new server name. The certificate is still valid for the new server, but has begun to stop working.

My solution is to delete my OWA and rebuild it with the new server name to match the certificate. Is this what yall would do?

The mistake I made a few years ago was that I put ourdomain.com as the SAN Cert name and that didn't like to play nice with the OA. We contacted the CA and they did a one time change on our cert to mail.ourdomain.com I re-imported like a new updated cert and it has been fine ever since.

BrianCFreeman, I believe so. My certificate is correct, but my OWA was from a migration from one server to another and OWA kept the legacy name. It doesn't affect it too much with OWA over the web, but when Outlook Anywhere gets involved, then the certificate does matter because Outlook will not connect if the certificate does not match the OWA Outlook is connecting to. Does that make sense or is it now clear as mud?

It is clear to me since I had a similar issue. It seems that my issue was backwards from yours but still the same principle. Hope you can get it fixed now that you know what the problem is!

You can manually set the Proxy Server info in the OA Connection Settings to match what they should be but since the cert is not matching you will get the cert warnings and possible connection issues. I would think the server name really needs to be changed to whatever the cert is. You could also look at a new cert that names your exchange box and then as stated by others above just use split DNS to circumvent the need for a SAN cert.

Hello! I work with NerdyDad. Neither of us are experts in this area, so thanks for your patience while we try and get this figured out. I've managed to export our Outlook Anywhere configuration from PowerShell, pasted below. Can anyone see anything wrong? BrianCFreeman: are you saying we should try to change either the Name or ServerName from the machine's local name to its FQDN? Thanks again.

Seth8589 and I fixed the issue by disabling and re-enabling Outlook Anywhere and configuring it as needed. We deleted our Outlook profiles and recreated them because they would have cache from the last installment, connected to a guest wireless network and it seemed to have fixed the problem. Thanks for all your help guys.